Synthesis of 2-azidoethyl α-D-mannopyranoside orthogonally protected and selective deprotections

Tetrahedron Letters

Volumn 47, Issue 15, 2006, Pages 2475-2478

  Reina, José Juan ^a   Rojo, Javier ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZIDOETHYL ALPHA DEXTRO MANNOPYRANOSIDE; GLYCOSIDE; MANNOSYL GLYCOSIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; GLYCOSYLATION; HYDROGENOLYSIS; SYNTHESIS;

EID: 33644917983     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.063     Document Type: Article

References (22)

1. Y. van Kooyk, and T.B.H. Geijtenbeek Nat. Immunol. 3 2003 697 709
2. T.B.H. Geijtenbeek, D.S. Kwon, R. Torensma, S.J. van Vliet, G.C.F. van Duijnhoven, J. Middel, I.L.M.H.A. Cornelissen, H.S.L.M. Nottet, V.N. KewalRamani, D.R. Littman, C.G. Figdor, and Y. van Kooyk Cell 100 2000 587 597
3. D.M. Ratner, O.J. Plante, and P.H. Seeberger Eur. J. Org. Chem. 2002 826 833
4. J. Zhang, Z. Ma, and F. Kong Carbohydr. Res. 338 2003 2039 2046
5. H.-K. Lee, C.N. Scanlan, C.-Y. Huang, A.Y. Chang, D.A. Calarese, R.A. Dwek, P.M. Rudd, D.R. Burton, I.A. Wilson, and C.-H. Wong Angew. Chem., Int. Ed. 43 2004 1000 1003
6. X. Geng, V.Y. Dudkin, M. Mandal, and S.J. Danishefsky Angew. Chem., Int. Ed. 43 2004 2562 2565
7. X. Schratt, and C. Unverzagt Tetrahedron Lett. 46 2005 691 694
8. D.A. Mitchell, A.J. Fadden, and K. Drickamer J. Biol. Chem. 276 2001 28939 28945
9. C.-H. Wong, X.-S. Ye, and Z. Zhang J. Am. Chem. Soc. 120 1998 7137 7138
10. T. Zhu, and G.-J. Boons Tetrahedron Asymmetry 11 2000 199 205
11. E. Arce, P.M. Nieto, V. Díaz, R. García Catro, A. Bernad, and J. Rojo Bioconjug. Chem. 14 2003 817 823
12. M. Kleinert, N. Rockendorf, and T.K. Lindhorst Eur. J. Org. Chem. 2004 3931 3940
13. X. Wu, and D.R. Bundle J. Org. Chem. 70 2005 7381 7388
14. R. Roy, D. Pagé, S. Figueroa Perez, and V. Verez Bencomo Glycoconj. J. 15 1998 251 263
15. J.B. Corbell, J.J. Lundquist, and E.J. Toone Tetrahedron Asymmetry 11 2000 95 111
16. T.K. Lindhorst, S. Kötter, U. Krallmann-Wenzel, and S. Ehlers J. Chem. Soc. Perkin Trans. 1 2001 823 831
17. D.K. Baeschlin, A.R. Chaperon, L.G. Green, M.G. Hahn, S.J. Ince, and S.V. Ley Chem. Eur. J. 6 2000 172 186
18. S. Cherif, J.-M. Clavel, and C. Monneret J. Carbohydr. Chem. 17 1998 1203 1218
19. N.-C. Reichardt, and M. Martín-Lomas Angew. Chem., Int. Ed. 42 2003 4674 4677
20. t-But).
21. S. Hanessian, and P. Lavallee Can. J. Chem. 53 1975 2975 2977
22. J.H. van Boom, and P.M.J. Burgers Tetrahedron Lett. 17 1976 4875 4878